Synthesis, chemistry and photochemistry of cyanobutadiyne (HCCCCCN)

Guillemin, Jean‐Claude; Trolez, Yann; Moncomble, Aurélien

doi:10.1016/j.asr.2007.08.013

Cited by 5 publications

(4 citation statements)

References 38 publications

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“…Our approach was limited on the preparative scale by a yield of only 15 % for the last step and was performed starting from 1,3-butadiynetributylstannane, a compound that can only be kept at À20 8C. [16] Its synthesis could be simplified by having the corresponding amide precursor in hand. Starting from commercially available 1,4-bis(trimethylsilyl)butadiyne, the corresponding ester 9 was obtained in 55 % yield by a first addition of MeLi·LiBr to form the corresponding monolithiated acetylide, which was then treated with an excess of methylchloroformate.…”

mentioning

confidence: 99%

Methylcyanobutadiyne: Synthesis, X‐ray Structure and Photochemistry; Towards an Explanation of Its Formation in the Interstellar Medium

Kerisit

Toupet

Trolez

et al. 2013

Chemistry A European J

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By deliberately using a metastable polyanion [(NbO2)6P2W12O56]12− (1), which was formed in situ, we have discovered the unprecedented hexameric cluster {Mn15(Nb6P2W12O62)6} (2), in which the six polyanions [Nb6P2W12O61]10− are alternately connected by four intriguing trinuclear {MnIII3} moieties and four {MnII} linkers. This discovery is the first in which the phosphoniobotungstate has been made accessible by using transition‐metal ions; furthermore, polyanion 2 represents the largest niobotungstate cluster reported to date. Analysis by means of electrospray ionization mass spectrometry (ESI‐MS) provides insight into the self‐assembly process, and the peaks observed relate to the different charge states of the parent cluster, thus confirming the stability of 2. In addition, magnetic‐susceptibility measurements reveal that each {MnIII3} subunit is a separate single‐molecule magnet (SMM). This discovery results from the exploration of the reverse effect of metastable polyanion 1 possessing high reactivity, thereby turning a disadvantage into an advantage. This finding could define a new synthetic strategy for the design and synthesis of magnetic polyoxometalate (POM) clusters.

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confidence: 99%

Methylcyanobutadiyne: Synthesis, X‐ray Structure and Photochemistry; Towards an Explanation of Its Formation in the Interstellar Medium

Kerisit

Toupet

Trolez

et al. 2013

Chemistry A European J

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“…Very few photolysis studies of HC 5 N exist. In the gas phase, attempts to detect products of HC 5 N photolysis at 254 nm have been unsuccessful, but dust attributed to the formation of oligomeric compounds was observed [ Guillemin et al , 2008]. In an Ar matrix at 10 K, Coupeaud et al [2007] demonstrated that photolysis at 267 nm of HC 5 N leads to the formation of isocyanodiacetylene (H‐C≡C‐C≡C‐N=C) with no other products being observed.…”

Section: Astrophysical Implicationsmentioning

confidence: 99%

Temperature‐dependent photoabsorption cross section of cyanodiacetylene in the vacuum UV

Fray¹,

Bénilan²,

Gazeau³

et al. 2010

J. Geophys. Res.

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[1] Using synchrotron radiation as a tunable VUV light source, we have measured, for the first time, the absolute photoabsorption cross sections of HC 5 N with a spectral resolution of 0.05 nm in the region between 80 and 205 nm from 233 to 298 K. The measured cross sections are used to predict the HC 5 N photodestruction rate in the solar system and to model a transmission spectrum in Titan's atmosphere. Comparing the latter with that acquired by the Ultraviolet Imaging Spectrograph on board the Cassini spacecraft, we have determined an upper limit of 2.7 × 10 −5 on the HC 5 N abundance at 1100 km.

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“…Our previous study of the addition of nucleophiles on cyanobutadiyne showed the exclusive formation of the 1,6addition products as a mixture of Z/E isomers. 6b, 30 In the present work, MeC 5 N has been treated with dimethylamine or morpholine in either methanol or tetrahydrofuran. For each experiment, 1 equiv of amine was added at room temperature; the compounds were reacted for 2 h, and the products were isolated after column chromatography.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis, Chemistry, and Photochemistry of Methylcyanobutadiyne in the Context of Space Science

et al. 2016

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An alternative preparation of methylcyanobutadiyne (MeC5N), a molecule present in the interstellar medium, was established in order to circumvent tedious steps from previous methods. The possibility of forming methylcyanoacetylene and MeC5N by gas-phase photolysis was evaluated from relevant acetylene derivatives in the context of space science. The reactivity of MeC5N toward simple nucleophiles was investigated. The exclusive formation of E adducts was observed, together with a solvent dependence for the regioselectivity of the addition.

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Synthesis, chemistry and photochemistry of cyanobutadiyne (HCCCCCN)

Cited by 5 publications

References 38 publications

Methylcyanobutadiyne: Synthesis, X‐ray Structure and Photochemistry; Towards an Explanation of Its Formation in the Interstellar Medium

Methylcyanobutadiyne: Synthesis, X‐ray Structure and Photochemistry; Towards an Explanation of Its Formation in the Interstellar Medium

Temperature‐dependent photoabsorption cross section of cyanodiacetylene in the vacuum UV

Synthesis, Chemistry, and Photochemistry of Methylcyanobutadiyne in the Context of Space Science

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